H. Akita et al., ENZYMATIC-HYDROLYSIS IN ORGANIC-SOLVENTS FOR KINETIC RESOLUTION OF WATER-INSOLUBLE ALPHA-ACYLOXY ESTERS WITH IMMOBILIZED LIPASES, Chemical and Pharmaceutical Bulletin, 45(2), 1997, pp. 272-278
Enantioselective hydrolysis of water-insoluble alpha-acyloxy esters, (
+/-)-5 and (+/-)-6, was carried out using lipases immobilized with Cel
ite or a synthetic prepolymer (ENTP-4000 or ENT-4000) in a water-satur
ated organic solvent to produce chiral intermediates, (2S,3S)-5 and (2
S,3R)-4, for the synthesis of diltiazem hydrochloride 1 and (-)-indolm
ycin 2, respectively, Furthermore, enantioselective hydrolysis of (+/-
)-6 using lipid-lipase aggregates in water-saturated organic solvent w
as also found to give (2S,3R)-4.